Title: Book the Best Hotels with POOL in Anna Maria Island in 2025 | Expedia.ca [Anna Maria Island Travel Guide](https://expedia.ca/Anna-Maria-Island.dx553248622847118534)[Hotels in Anna Maria Island](https://expedia.ca/Anna-Maria-Island-Hotels.d553248622847118534.Travel-Guide-Hotels)[Vacation Rentals in Anna Maria Island](https://expedia.ca/Anna-Maria-Island-Vacation-Rentals.d553248622847118534.Travel-Guide-VacationRentals)[Flights to Anna Maria Island](https://expedia.ca/Cheap-Flights-To-Anna-Maria-Island.d553248622847118534.Travel-Guide-Flights)[Things to do in Anna Maria Island](https://expedia.ca/Things-To-Do-In-Anna-Maria-Island.d553248622847118534.Travel-Guide-Activities)[Anna Maria Island Car Rentals](https://expedia.ca/Car-Rentals-In-Anna-Maria-Island.d553248622847118534.Car-Rental-Guide)[Anna Maria Island Vacation Packages](https://expedia.ca/Anna-Maria-Island.d553248622847118534.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/6e0a40c600747ff11aa2868df9ff0b93.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Anna Maria Island, FL ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Anna Maria Island Hotels with a Pool Tonight [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-24&endDate=2025-10-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-25&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248622847118534&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Anna Maria Island Hotels with a Pool ![Outdoor pool](https://images.trvl-media.com/lodging/121000000/120120000/120114200/120114144/c4463db9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120120000/120114200/120114144/459a56f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo](https://images.trvl-media.com/lodging/121000000/120120000/120114200/120114144/1b0e5d4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, white sand](https://images.trvl-media.com/lodging/121000000/120120000/120114200/120114144/0d4c4896.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Alamanda Villas Holmes Beach 10/10 Exceptional (2) "The location is wonderful for beach access,places to eat and grocery is block away. Small parking area if more than one couple stay. Had a great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Traci CA $320 CA $643 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Holmes-Beach-Hotels-Alamanda-Villas.h120114144.Hotel-Information) ![Outdoor pool, a heated pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/6000000/5420000/5411200/5411119/c5486eb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, white sand, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/6000000/5420000/5411200/5411119/def997fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/6000000/5420000/5411200/5411119/4caa2fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5420000/5411200/5411119/33da3e6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palm Tree Villas Holmes Beach 9.2/10 Wonderful (172) "Lovely property, clean and so close to the beach! Do need a car, for food/dinning. We'll be back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nadya CA $189 CA $423 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Sarasota-Hotels-Palm-Tree-Villas.h5411119.Hotel-Information) ![Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/900000/897700/897646/d776e9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/1000000/900000/897700/897646/577e4a42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, individually decorated](https://images.trvl-media.com/lodging/1000000/900000/897700/897646/1e58e697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, white sand, sun loungers, beach towels](https://images.trvl-media.com/lodging/1000000/900000/897700/897646/fc900ac2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Haley's at The Anna Maria Island Inn Holmes Beach 8.6/10 Excellent (380) "The staff members were so nice and super helpful!! Place was so cute! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Whitley CA $236 CA $299 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Sarasota-Hotels-Haleys-Couples-Retreat.h897646.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/84000000/83510000/83500900/83500895/0ce71205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/84000000/83510000/83500900/83500895/e64ffac1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/84000000/83510000/83500900/83500895/8927606c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/84000000/83510000/83500900/83500895/b209e6c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Retreat at Anna Maria Island Inn Bradenton Beach 9.4/10 Exceptional (26) "Beautiful room, convenient location, and excellent service! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bianca CA $236 CA $299 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Bradenton-Beach-Hotels-The-Retreat-At-Anna-Maria-Island-Inn.h83500895.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/ce1b2724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King Room | Living area](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/12fee06e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch Smart TV with digital channels, TV](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/2d6f0d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/4174e2ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pelican Post at Anna Maria Island Inn Bradenton Beach 9.2/10 Wonderful (311) "Great location, nice rooms, relaxing pool area. Walkable to Bridge Street and the beach." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela CA $266 CA $337 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Sarasota-Hotels-Pelican-Post.h67676083.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/36000000/35100000/35093800/35093744/2055d637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/36000000/35100000/35093800/35093744/a5adbfe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35100000/35093800/35093744/177ae5b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35100000/35093800/35093744/23e0c0f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacay in Luxury! 2 mins to the Beach! Holmes Beach 9.8/10 Exceptional (65) "Very nice, very close to beach. Only negative was no dresser or shelf for clothes. Had to live out of suitcase. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin H. CA $175 CA $448 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Holmes-Beach-Hotels-Vacay-In-Luxury-So-Close-To-The-Beach.h35093744.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/933a3ccd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/cc175788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/ebba9faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70580000/70579400/70579361/19ccb378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand! Anna Maria 10/10 Exceptional (35) "Perfect, cutest cottage within steps of the beach." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joni M. CA $250 CA $663 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Anna-Maria-Hotels-Anna-Maria-Beach-Cottage-110b-Updated-Studio-Beach-Cottage.h70579361.Hotel-Information) ![Outdoor pool, open 8:00 AM to 8:00 PM, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/37000000/36290000/36286200/36286167/9cd29b87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/37000000/36290000/36286200/36286167/f990b212.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/37000000/36290000/36286200/36286167/14f9d1d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Beachside 1 Bedroom King Suite | Living area](https://images.trvl-media.com/lodging/37000000/36290000/36286200/36286167/37def3a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bali Hai Beachfront Resort and Spa Holmes Beach 8.6/10 Excellent (623) "Easy parking (even go golf carts!) Perfect location, and staff was super helpful and accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $354 CA $449 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Sarasota-Hotels-Bali-Hai-Beach-Resort.h36286167.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/95000000/95000000/94993900/94993833/f850ee3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/95000000/95000000/94993900/94993833/288b4afd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/95000000/95000000/94993900/94993833/c469cd38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room](https://images.trvl-media.com/lodging/95000000/95000000/94993900/94993833/78542cef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Driftwood at Anna Maria Island Inn Holmes Beach 8.4/10 Very good (70) "Absolutely beautiful room, quiet, close walk to the beach, and an affordable price. Will be staying here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert A CA $220 CA $279 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Holmes-Beach-Hotels-Driftwood-At-Anna-Maria-Island-Inn.h94993833.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/60000000/59790000/59789500/59789467/651a8200.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/60000000/59790000/59789500/59789467/c2dde255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/60000000/59790000/59789500/59789467/5f1d6b2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/60000000/59790000/59789500/59789467/85b3dcb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captain's Quarters at Anna Maria Island Inn Bradenton Beach 9.2/10 Wonderful (20) "Lovely place every thing in walking distance And the beach was across the road We would stay here again" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Carole CA $281 CA $355 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Sarasota-Hotels-Captains-Quarters-By-AMI-Locals.h59789467.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-08®ionId=553248622847118534&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Anna Maria Island Hotel Reviews ![Tortuga Inn Beach Resort](//images.trvl-media.com/lodging/2000000/1060000/1054200/1054101/b1d10d73_y.jpg) ### Tortuga Inn Beach Resort 10/10 Excellent "Front office staff were very friendly and the place was very clean." [](https://expedia.ca/Sarasota-Hotels-Tortuga-Inn-Beach-Resort.h1054101.Hotel-Information) ![Silver Surf Gulf Beach Resort](//images.trvl-media.com/lodging/2000000/1050000/1045900/1045895/12fa4f1f_y.jpg) ### Silver Surf Gulf Beach Resort 10/10 Excellent "Love the Silver Surf! Friendly staff, spacious clean rooms, and beautiful beach. We stay there every time we go to AMI!" [](https://expedia.ca/Sarasota-Hotels-Silver-Surf-Gulf-Beach-Resort.h1045895.Hotel-Information) ![Haley's at The Anna Maria Island Inn](//images.trvl-media.com/lodging/1000000/900000/897700/897646/fc900ac2_y.jpg) ### Haley's at The Anna Maria Island Inn 10/10 Excellent "This was our 1st time in Anna Maria. It was a nice little beach town. The hotel was all renovated and really nice! Great location to everything. Easy walk down to the beach, and restaurants and shops super close as well. We enjoyed our stay here and would definitely come back! 😊 " [](https://expedia.ca/Sarasota-Hotels-Haleys-Couples-Retreat.h897646.Hotel-Information) ![Seabreeze at Anna Maria Island Inn](//images.trvl-media.com/lodging/17000000/16010000/16001900/16001812/a71dc126_y.jpg) ### Seabreeze at Anna Maria Island Inn 10/10 Excellent "Family friendly" [](https://expedia.ca/Sarasota-Hotels-Anna-Maria-Island-Inn.h16001812.Hotel-Information) ![Bridgewalk Resort](//images.trvl-media.com/lodging/2000000/1050000/1045900/1045894/7186dbd7_y.jpg) ### Bridgewalk Resort 10/10 Excellent "There is nothing I could possibly complain about. The room, parking, location, staff everything was absolutely perfect. " [](https://expedia.ca/Sarasota-Hotels-Bridgewalk-A-Landmark-Resort.h1045894.Hotel-Information) ![Tropic Isle at Anna Maria Island Inn](//images.trvl-media.com/lodging/2000000/1610000/1602500/1602498/d3036c76_y.jpg) ### Tropic Isle at Anna Maria Island Inn 8/10 Good "I reported the AC wasn't working 3 times and nobody fix the problem for my request " [](https://expedia.ca/Sarasota-Hotels-Tropic-Isle-At-Anna-Maria-Island-Inn.h1602498.Hotel-Information) ![Waterline Villas & Marina, Autograph Collection](//images.trvl-media.com/lodging/16000000/15740000/15739500/15739491/c50d8ef8_y.jpg) ### Waterline Villas & Marina, Autograph Collection 10/10 Excellent "Exceptional " [](https://expedia.ca/Sarasota-Hotels-Waterline-Marina-Resort-Beach-Club.h15739491.Hotel-Information) ![Tradewinds Beach Resort](//images.trvl-media.com/lodging/2000000/1150000/1146400/1146353/6dd9a7bc_y.jpg) ### Tradewinds Beach Resort 10/10 Excellent "Very cute place and easy to walk to beach " [](https://expedia.ca/Sarasota-Hotels-Tradewinds-Beach-Resort.h1146353.Hotel-Information) ## Explore a world of travel with Expedia - 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[Hotels with Hot Tubs in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Hotels-With-Hot-Tubs.0-n553248635976473287-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Luxury-Hotel.0-n553248635976473287-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Mountain-Hotels.0-n553248635976473287-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Oceanfront-Hotels.0-n553248635976473287-0-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Pet-Friendly-Hotel.0-n553248635976473287-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Orange Lake](https://www.expedia.ca/Orange-Lake-Orlando-Hotels-Waterpark-Hotels.0-n553248635976473287-0-tWaterparkHotels.Travel-Guide-Filter-Hotels) - 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